Lily observes the traffic on Fifth Avenue, and sees Mrs. Van Osburgh, Evie, and the latter's new infant. She also sees Mrs. Hatch and Judy. Lily has been laid off from Mme. Regina's shop, a fate that she had anticipated.
Rosedale visits Lily. He offers to loan her the money to repay Trenor, but she refuses, telling Rosedale that she has nothing to secure the loan. He tells her that he is leaving for Europe for a period of several months, and would like to help her. He renews his offer to marry her with the implied provision that she set aside her differences with Bertha. Lily is touched by his declaration that he could position her where she "could wipe [her] feet on 'em!"
Lily considers using the letters to convince Bertha to allow Lily's return to society. The following morning, she devises her plan at a restaurant on Fifty-ninth Street. She goes home to retrieve the letters, and then heads to Bertha's home. On her way, however, she passes the street where she had strolled with Selden two years prior. She considers how Selden would judge her intended action to blackmail Bertha. She sees a light in Selden's apartment and enters his building.
Lily contemplates the differences between beauty in nature and beauty in society. Social beauty, she believes, is hampered by material desire and moral scruples. She chafes at what Wharton describes as the "selfish despotism of society." Lily realizes that she lacks the moral constancy to succeed as a working-class woman, and admits that she is nostalgic for the life of the idle rich.
Lily considers her relationship with Selden, and realizes that she has squandered the love he once harbored for her. She also realizes that she has employed Selden as a moral compass in the past and once again gauges her actions according to his opinion of her.